((E)-2-((R,Z)-6-(4-methoxybenzylidene)tetrahydro-2H-pyran-2-yl)vinyl)trimethylsilane

Base Information

• Chemical Name: ((E)-2-((R,Z)-6-(4-methoxybenzylidene)tetrahydro-2H-pyran-2-yl)vinyl)trimethylsilane
• CAS No.: 1569091-28-6
• Molecular Formula: C₁₈H₂₆O₂Si
• Molecular Weight: 302.489
• Mol file: 1569091-28-6.mol

Synonyms:((E)-2-((R,Z)-6-(4-methoxybenzylidene)tetrahydro-2H-pyran-2-yl)vinyl)trimethylsilane

Chemical Property of ((E)-2-((R,Z)-6-(4-methoxybenzylidene)tetrahydro-2H-pyran-2-yl)vinyl)trimethylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((E)-2-((R,Z)-6-(4-methoxybenzylidene)tetrahydro-2H-pyran-2-yl)vinyl)trimethylsilane

There total 4 articles about ((E)-2-((R,Z)-6-(4-methoxybenzylidene)tetrahydro-2H-pyran-2-yl)vinyl)trimethylsilane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 45.0%

((E)-2-((Z)-6-(4-methoxybenzylidene)tetrahydro-2H-pyran-2-yl)vinyl)trimethylsilane (1569092-04-1) → ((E)-2-((R,Z)-6-(4-methoxybenzylidene)tetrahydro-2H-pyran-2-yl)vinyl)trimethylsilane (1569091-28-6)

Guidance literature:

With (S)-4-tert-butyl-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-1,3-oxazol; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In dimethyl sulfoxide; at 40 ℃; enantioselective reaction; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1039/c4cc00109e

Reference yield:

((E)-2-((Z)-6-(4-methoxybenzylidene)tetrahydro-2H-pyran-2-yl)vinyl)trimethylsilane (1569092-04-1) → ((E)-2-((R,Z)-6-(4-methoxybenzylidene)tetrahydro-2H-pyran-2-yl)vinyl)trimethylsilane (1569091-28-6) + C18H26O2Si (1569091-12-8) + C18H26O2Si

Guidance literature:

With (S)-4-tert-butyl-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-1,3-oxazol; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In dimethyl sulfoxide; at 40 ℃; for 1h; enantioselective reaction; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1039/c4cc00109e

Reference yield:

(2-(6-methoxytetrahydro-2H-pyran-2-yl)vinyl)trimethylsilane → ((E)-2-((R,Z)-6-(4-methoxybenzylidene)tetrahydro-2H-pyran-2-yl)vinyl)trimethylsilane (1569091-28-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetonitrile / 4 h / 25 °C / Molecular sieve; Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: bis(dibenzylideneacetone)-palladium⁽⁰⁾; (S)-4-tert-butyl-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-1,3-oxazol / dimethyl sulfoxide / 40 °C / Schlenk technique; Inert atmosphere; Sealed tube

With (S)-4-tert-butyl-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-1,3-oxazol; lithium hexamethyldisilazane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; dimethyl sulfoxide; acetonitrile; 2.1: |Wittig Olefination / 2.2: |Wittig Olefination;

DOI:10.1039/c4cc00109e

upstream raw materials:

((E)-2-((Z)-6-(4-methoxybenzylidene)tetrahydro-2H-pyran-2-yl)vinyl)trimethylsilane